Methanol → HCID 136158584, compound

Participants

Reaction Steps

Add a 1.0 M solution of boron tribromide (2.31 L, 2.31 mol) in dichloromethane (1.87 L) to a cold (0° C.) solution of 6-fluoro-3-(4-methoxy-phenyl)-benzo[d]isoxazole (187.2 g, 0.77 mol) in dichloromethane, over ˜2 hours. Warm to room temperature overnight. Cool reaction mixture to ˜3° C. and add methanol (4 L) over a period of time of 1 hour, keeping the temperature of the reaction mixture at 3-10° C. Gas evolution occurs. Concentrate (40-50° C., 50 torr) reaction mixture to give a gray solid. Heat to dissolve the gray solid in isopropyl alcohol (550 mL) at reflux. Cool (room temperature), followed by 0-5° C. for 1 hour. Filter off the solid and wash filter cake with cold (0° C.) isopropyl alcohol (265 mL) and dry to air. Subsequently dry the solid in the oven (60° C., 50 torr) overnight to give the title compound (147.2 g, 83% Yield): 1H NMR (DMSO-d6, 200 MHz) δ 7.0 (d, 2H), 7.4 (t, 1H), 7.8 (d, 1H), 7.84 (d, 2H), 8.18 (m, 1H). Purity by LC/MS (APCl)=100% area, [M+H]+=230 m/e.

Provenance & Evidence